(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

Base Information

Chemical Name:(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose
CAS No.:1332506-86-1
Molecular Formula:C₁₇H₂₅FO₂Si
Molecular Weight:308.468
Hs Code.:

Synonyms:(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

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Chemical Property of (-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

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Technology Process of (-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

There total 3 articles about (-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 1332506-77-0
(2R,1'S)-tert-butyl(dimethyl)(2-(1'-(3''-fluorophenyl)allyloxy)-but-3-enyloxy)silane

: 1332506-86-1
(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 40 ℃; for 5h; Inert atmosphere;
DOI:10.1021/jo201110z

Reference yield:

: 119125-28-9,136917-96-9,136984-28-6
(R)-1-(tert-butyldimethylsilyloxy)but-3-en-2-ol

: 1332506-86-1
(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; pentane / 0.25 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

1.3: 16 h / 0 - 20 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 5 h / 40 °C / Inert atmosphere

With Grubbs catalyst first generation; n-butyllithium; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/jo201110z

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1332506-86-1
(-)-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-1',2',3'-trideoxy-1'-(3-fluorophenyl)-β-L-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; pentane / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

2.3: 16 h / 0 - 20 °C / Inert atmosphere

3.1: Grubbs catalyst first generation / dichloromethane / 5 h / 40 °C / Inert atmosphere

With Grubbs catalyst first generation; dmap; n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/jo201110z